My First Time

This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback…

I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too many one nighters to tally up. Up until recently I have always been a guy exclusively into women, natural born female variety. Sure, probably like most guys, I have considered other options but always recoiled at the thought of getting it on with another guy. Oh God no, I could never do that! I kind of always thought, I can understand why girls want to be with other girls, but how can chicks ever possibly really be into men? We are not attractive. So yeah, I guess that made me pretty much heterosexual as you can get. Well, I always liked cocks. I said liked, not licked, get your mind out of the gutter. So there was always hope for change? Maybe.

So lots of women had come and gone (yes, and cum) and I guess I was getting bored of all that action. Maybe I needed something more. Something I had not yet discovered. Hindsight is a wonderful thing, as they say, and it allowed me to realise that I had never actually been in love with any of those women. Maybe now I needed a relationship to help me to grow as a person after becoming tired of all the conquering that went before. Maybe I just needed a change of some sort, some new interests or something like that.

I had been aware of transgender women for a long time, however, I had not really paid any real attention. I guess my relatively narrow minded approach to my sexuality left me thinking, despite an interest in a good looking girl with a dick, that was too close to liking men and that just wasn’t going to happen. One day I was surfing around online looking for some inspirational material that was going to help me with some DIY, if you know what I mean. I had actually been jumping around many different tube sites starting then skipping many videos.